


A Pocket Full of Panties (We All Fall Down)

by chemically_yours



Category: Supernatural
Genre: Anal Sex, Destiel - Freeform, Explicit Sex, M/M, Panty Kink, Vermont Thong, cas is a good boyfriend, sam is an oblivious moose, vong
Language: English
Status: Completed
Published: 2017-03-17
Updated: 2017-03-17
Packaged: 2018-10-06 09:21:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,587
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10331465
Author URL: https://archiveofourown.org/users/chemically_yours/pseuds/chemically_yours
Summary: In which Castiel tries to be a good lover but misses the mark, Dean makes the most of the situation, and Sam learns something new.





	

**Author's Note:**

> So Levisarelamprey on tumblr made the mistake of texting me during work asking for headcannons on the various clothing fetishes of the Winchesters. It was a slow day and the end result of the conversation was a condensed version of this fic. 
> 
> Levisarelamprey is a wonderful beta (and even more wonderful friend) that reads all my fics and puts up with my nonsense and in return I have decided to give her the gift of porn. Thanks for all your hard work. <3

 

 

A Pocket Full of Panties (We All Fall Down)

 

 

Castiel stared at the store front display set behind the large tinted window. He was aware of the people giving him a wide berth on the sidewalk, shooting him quizzical and disapproving stares as they hurried past. He ignored them all. He was battling indecision as a memory from several weeks prior flowed through him.

He thought of Dean’s whispered confession, rushed and tinged with embarrassment as they lay tangled together. Human sexuality was a fascinatingly complex thing that he had only recently begun to experience. Dean had been forthcoming in some areas but reticent in others. Castiel still didn’t understand why some things were allowed to be talked about openly and with pride while others were sources of embarrassment. It all seemed rather arbitrary with a set of rules that had no logic that Castiel could understand. Nonetheless, he was determined to learn all he could so as to be a better lover.

Currently, Castiel was supposed to be helping Sam and Dean hunt down a cursed artifact that had been plaguing the people of this town. But the store had caught his attention and Dean’s nervous fidgeting and bright blush flooded his mind. Surely…surely it would be okay if he took a short break? It shouldn’t take more than five minutes to procure what he needed. And he wasn’t having much luck hunting down the artifact anyway. It wasn’t at the church he had searched so it was likely Sam or Dean would be the ones to find it. He’d stop in just real quick. It was for Dean, after all.

...

Dean flopped back on the bed, utterly exhausted from this latest hunt. They’d gone in thinking it was a haunting and wound up having to hunt down a stupid cursed lava lamp. Who the hell cursed a lava lamp?

Sam was still out and about tying up loose ends. He’d told Dean he probably wouldn’t be back for a couple hours, which meant that if Cas would hurry and get his feathered ass back here they’d be able to enjoy a little alone time for once. As if summoned by this thought, Cas arrived back carrying a paper shopping bag with some chic lettering on the side. He carefully latched the door behind him and checked to make sure the blinds and curtains were drawn closed before finally making his way over to the bed Dean was lounging on. Dean grinned; apparently they were on the same page. They spent several long moments kissing each other in greeting, gentle and easy. Eventually, Cas moved away to grab the bag he’d placed on the edge of the bed. Dean sat up as his curiosity was piqued. Cas wasn’t looking at him, instead choosing to focus on the bag he now gripped tightly in both hands. His nerves proved to be infectious. Apprehension curled tightly in Dean’s stomach. What in the world was his angel up to?

“Dean. I’ve brought you a. A present. Of sorts. It’s. Well, you had mentioned, so I. Here.”

Cas finally handed the crumpled bag over. Dean tore into the tissue paper inside, eager to know what kind of gift would make Cas this nervous. His fingers found a patch of cotton and he finally pulled the item out, holding it up between them in triumph. There was a pause while his brain caught up with what his eyes were seeing. His mouth dropped open in shock as he struggled to comprehend that why yes, he was holding up a thong. A flannel thong. A plaid flannel thong. Why was this a thing that existed and where did someone buy something like this? What the hell?

Cas interrupted by clearing his throat in clear discomfort. “I thought you might like to wear it. You said you enjoyed women’s undergarments. The sales woman assured me that this brand is very comfortable and fashionable around this area.”

Dean continued to gape in bewilderment, only snapping out of it when Cas began to frown, clearly dejected by the reaction his gift had garnered. Dean shook his head and reached out to clasp Cas’s hands in his, forcing his face into an approximation of a smile. Cas was making an effort to be thoughtful and Dean needed to show his appreciation. He shouldn’t blow this off. It was clearly important to Cas that Dean like the present.

“Cas. This is. This is really…something. I’m sorry, I’m just really surprised. I wasn’t expecting anything like this. But this is… Thank you.”

The tension drained out of Cas at the reassurance, and Dean felt himself relax too. They were okay. Dean reeled Cas in for some more kissing. Sam wouldn’t be gone forever so it was time to get this show on the road. Things proceeded quickly and it wasn’t long before shirts had been discarded. Dean reached for Cas’s belt, only to have his hands knocked away.

“Why don’t you go put on your present?”

Dean tried to stammer out a response but in the end could only nod his head and stagger into the bathroom to change. Fumbling, it took him longer than it should have to get his pants off. He hadn’t expected Cas to want him in the panties tonight, or ever. He’d really been hoping he could just wear them once to say he had and then unfortunately lose them and never have to see the monstrosity again. But when Cas made up his mind to take interest in Dean’s interests, he became invested. Dean knew he was lucky. There weren’t a whole lot of people that would have been as understanding about the kinds of things he was into. Really, Cas being invested and actually wanting to participate was more than Dean would have ever hoped for. He’d been expecting cool disinterest at most. If Cas was willing to indulge in Dean’s peculiarities, then Dean needed to show his appreciation, even if Cas had landed a little off the mark. He took a deep breath to settle his nerves and studied the garment in his hands.

It seemed impossibly smaller as he examined the tiny triangle of fabric. He’d never worn a thong before, never quite been that daring. Most of the lacey and silky things he’d worn in the past he could pretend were super fancy briefs when he was wearing them. He took a deep breathe to steady himself and quickly slipped them on before he could think of anything more beyond “this is for Cas.”

It took some adjustment, but he finally managed to get everything settled. He stared down a long moment at the head of his erection poking up over the top of the elastic band. He swallowed thickly, saliva suddenly as heavy as molasses. God, he hoped this was what Cas wanted. He didn’t want Cas to regret deciding to indulge Dean’s interests.

Dean returned to the room to find that Cas was now naked and waiting for him on the bed. He didn’t immediately react except to beckon Dean closer. Dean obliged, eyes to the floor, full-body flush heating his skin. He allowed himself to be pulled down on top of the angel.

“You look lovely,” Cas rasped out, before turning his attention to devouring Dean’s mouth. Dean shifted up to fully straddle Cas, the compliment making him harder and hotter. The thong nestled in between his asscheeks and he fought against the urge to reach back and relieve the wedgie. He ground his hips down, desperate to move away from the discomfort. Cas gasped around his tongue as their dicks were brought together again and again. The flannel was the only thing that was separating their flesh, and though it wasn’t quite the texture Dean usually went for with panties, he couldn’t help the whine that escaped his lips. The thong really wouldn’t be so bad if only it didn’t remind him of Sam’s shirt.

Cas moved his hands down to Dean’s ass. His fingers found the straps at his hips and traced them slowly to the center. Cas followed the strap down between Dean’s cheeks, brushing the fabric up against his hole. Dean pulled back and panted hotly onto Cas’s neck. He started to ask about lube, but Cas beat him to it by hauling Dean up into his lap while he sat up and reached for the bottle he had put on the nightstand. Good thing Cas was so good at thinking ahead. Finally, the irritating strap was pulled away and replaced by wet fingers. Dean murmured encouragement while sucking hickeys onto Cas’s collarbone, desperation taking hold of his thoughts at the first intrusion. The thong had become damp with sweat and precome, making it more annoying than anything. Dean hoped Cas would let him take it off for the actual sex. Flannel wasn’t the sexiest material.

Cas had other ideas. As soon as Dean was ready, he shoved him to the side and then up to all fours. Dean groaned as gravity battled with the elastic band of the thong over the weight of his swollen dick. Cas knelt behind him and gently pulled the strap to the side. The gift was clearly to remain on. Conflicting emotions battled in Dean as he struggled to figure out if the discomfort of wearing the heavy flannel on his cock was enough to outweigh the erotic knowledge that Cas was about to fuck him while he wore a thong.

The first hard press of Cas inside Dean lit him up from the inside, set his whole body ablaze. Dean gasped and fisted the sheets, needing to cling to something while Cas slowly pulled out and pushed back in. He kept things slow until Dean was spreading his legs wider and pushing back, frantic for more. Cas stopped, fully seated inside Dean, and pulled the strap even further to the side. He reached down to get a feel of Dean’s dick and the precome that was leaking down and soaking the front of the thong. The stupid thing was probably going to be ruined. He squeezed Dean gently through the fabric.

“Please. Cas, please. Give it to me. Nice and hard and faasss”

Dean didn’t get to finish as Cas finally took pity and started fucking him in earnest. Dean cried out with every thrust as spots danced in his vision. Each stab of pleasure brought him closer to the edge. The fabric between his legs ceased to be a discomfort as he finally managed to settle into the right frame of mind. This was for Cas. He was wearing the thong for Cas because Cas wanted to see him in it. He was doing good. All for Cas. Always for Cas.

Cas stared to stroke him through the flannel and that was it. Pleasure exploded out in waves and he was coming and coming. He wasn’t even aware of Cas finishing until he pulled out and Dean finally collapsed fully onto the bed. The roaring in his head faded as sensation came back. The front of the thong was now a sopping, sticky mess. Dean flopped over onto his back and peeled the offending clothing away and threw it somewhere between the bed and the wall. Cas reappeared with a damp washcloth. They cleaned up and then lay together in naked bliss. Dean kept one eye on the clock, knowing they’d have to get dress soon. He’d just cuddle with Cas for a few minutes.  
…

The next day saw the boys packing up to get back on the road. Sam had been out much later than he’d been planning last night and he wearily picked up their supplies and shoved them in duffle bags while he waited for Dean to return with coffee and breakfast for the trip. He was doing a last sweep of the room when his eyes caught on a piece of plaid fabric sticking out under the corner of Dean’s bed. He huffed out an exasperated breath. Leave it to Dean to somehow misplace his shirt under the bed.

Sam had enough time to register that the clothing is much lighter than he’d been expecting but it didn’t click why that was until he’s standing all the way up looking in dismay at the thong in his hand. He felt his mouth fell open in shock. When the hell had Dean found time to pick up a chick and get laid. Sam had thought Cas had been hanging around all night, but maybe he had gone out as well last night?

Sam knew he should be throwing the panties away in disgust and horror, but he couldn’t seem to pry his eyes away from the sight of the stained flannel. He was pretty sure he had a shirt in that exact shade. He didn’t know they made plaid thongs, but he couldn’t help the picture that was forming in his mind. It wasn’t hard to imagine. The woman in his head was an anonymous brunette with half-formed features wearing the thong and his shirt with nothing underneath. The shirt would be unbuttoned, but pulled closed enough to hide her breasts, leaving nothing but a teasing peak at her cleavage. She’d be giggling even as he pulled her down onto the bed with him and pulled her up to bracket her knees on either side of his head.

He was still standing there, staring at the thong with the beginnings of arousal, when Dean came walking back in with a cardboard tray of coffee. Dean paused mid-step and stared at Sam holding the panties and Sam wasn’t sure which of them is more horrified in that moment. Sam stared at Dean like a moose in headlights and Dean continued to stare back with the tray in his hand shaking. Sam tried desperately to think of something to say that didn’t involve confessing that he was getting turned on by weird lumberjane fantasies involving his brother’s one night stand’s thong. God, that sounded so creepy.

Sam was spared from having to say anything at all by the arrival of a donut-bearing Cas. Cas looked at Sam and Dean looking at each other and then he spotted the dirty panties in Sam’s hand. His expression brightened and he walked over to pluck them out of Sam’s palm, placing the donuts on the table in the process.

“Ah. I was wondering where these went.”

He zipped the panties up into the side pocket on Dean’s duffle then hauled the whole bag over his shoulder and headed down to the Impala, completely unaware of the stifling awkward silence he left behind. Dean had turned a brilliant shade of red and he made a strangled choking noise. Sam continued to gape.

“Um,” Sam finally managed to get out.

“Uh,” Dean replied.

They stared a beat longer until a silent, mutual agreement was reached to ask no questions. Sam took a deep breath and grabbed a donut to occupy his mouth with. He tried to remember what a normal morning routine involved. What would they have been doing without the interruption?

“Impala’s all gassed up and ready to go?” Sam asked in the steadiest voice he could manage. Dean nodded and very pointedly did not meet Sam’s eyes. He turned around and marched down to the driver’s seat. Cas was already seated in back. Sam climbed in with the donuts and they were on their way.

It was the longest drive of their lives.

**Author's Note:**

> BTW the vermont thong, or vong, is totally real: http://vermontflannel.com/vong.html


End file.
